Regiospecific formation of sugar-derived ketonitrone towards unconventional C-branched pyrrolizidines and indolizidines. Issue 29 (12th July 2019)

• Record Type: Journal Article
• Authors: Massicot, Fabien; Messire, Gatien; Vallée, Alexis; Vasse, Jean-Luc; Py, Sandrine; Behr, Jean-Bernard
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 29(2019)
• Page Start: 7066
• Page End: 7077
• Publication Date: 2019-07-12
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob01419e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The synthesis of unprecedented branched pyrrolizidines and indolizidines was accomplished via nitrone chemistry. Abstract : The synthesis of unprecedented branched pyrrolizidines and indolizidines was accomplished via nitrone chemistry. The required ketonitrone, a known intermediate usually obtained as a mixture of regioisomers, was prepared in a pure form fromd -arabinose by a sequence of oximation/reduction/oxidation steps. Nucleophilic vinylation or allylation followed by ring-closing metathesis of the corresponding N -allylpyrrolidines furnished the targeted iminosugars, which proved potent and selective inhibitors of alpha-glucosidase from rice (GH31 family).